A conventional approach to generate phosphonates relies on the Michaelis-Arbuzov rearrangement. This reaction is one of the most extensively investigated and well-known reactions in organic chemistry. First discovered by Michaelis in 1898, this reaction has provided an efficient and direct entry into phosphonate systems.
Specifically, the formation of dihydrocarbyl hydrocarbonphosphonates in the Michaelis-Arbuzov rearrangement relies on the reaction of a trialkyl phosphite with an alkyl halide in the presence of a transition metal salt as a catalyst. Today, many commercially available phosphonate chemicals are made with this technology, including dimethyl methanephosphonate. However, this methodology presents problems in its current practice. In some instances, this reaction is economically infeasible due to the required use of alkyl halides and the transition metal catalysts. Additionally, environmental concerns, such as ozone depletion, may be raised by this method of producing phosphonates. Further, these reactions often require temperatures in excess of 100° C., and tend to be exothermic in nature. It would be desirable if a new way could be found to produce dihydrocarbyl hydrocarbonphosphonates which minimizes without the problems or shortcomings just described.